Enzyme‐analogue built polymers, 4. On the synthesis of polymers containing chiral cavities and their use for the resolution of racemates

Abstract

Abstract With the aid of a chiral template molecule functional groups could be placed in a highly crosslinked polymer in such a way that they are present in a chiral cavity in a given stereochemistry. By this method methyl, resp. 4‐nitrophenyl α‐ D ‐mannopyranoside‐2,3; 4,6‐di‐ O ‐(4‐vinylphenylboronate) ( 1a , resp. 1b ) were copolymerized to macroporous polymers from which the templates methyl, resp. 4‐nitrophenyl α‐ D ‐mannopyranoside ( 2a , resp. 2b ) could be split off in return. It could be shown that such polymers with two boronic acid groupings within the chiral cavity possess a good ability for the resolution of racemates of the template used. In the case of the separation of the enantiomers of 2b separation factors up to 2,27 could be obtained. The overall optical enrichment in a chromatographic separation amounted to 87%.